Pseudoomphalina kalchbrenneri is a Eurasian species. In North America the Pso. kalchbrenneri complex is represented by Pseudoomphalina anticostica sp. nov. and Pso. compressipes in the east and Pso. intermedia in the west. Pseudoomphalina farinacea and Pso. felleoides are later synonyms for Pso. compressipes. The somewhat similar Pseudolaccaria pachyphylla occupies a temperate band through Eurasia, confirmed by sequencing in both eastern and western North America. It differs from species of the Pso. kalchbrenneri complex by smaller size, finely granular pileus, non-decurrent gills, and lack of hymenial cystidia. All species of the Pso. kalchbrenneri complex are uncommon, and macroscopically similar. Pseudoomphalina kalchbrenneri and Pso. intermedia can be identified by their distribution (Europe and western North America, respectively) and lack of cystidia. The cystidiate eastern North American Pso. anticostica and Pso. compressipes can be differentiated by the smaller spores of the latter. Pseudoomphalina cokeri is the most ancestral species on the Pseudoomphalina lineage, while Clitocybe thujana and Agaricus apertus (Clitocybe/Clitocybula aperta) fall outside Pseudoomphalina and Pseudolaccaria. We add 21 new sequences to GenBank, including six types (Agaricus compressipes, Clitocybe felleoides, C. farinacea, C. intermedia, C. thujana, Agaricus apertus), and one new species (Pso. anticostica).